3-Ethyl-6-(4-fluoro-phen-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazine.

In the title compound, C(12)H(11)FN(4)S, the thia-diazine ring adopts a twist-boat conformation. The dihedral angle between the triazolothia-diazine system and the benzene ring is 10.54 (9)°. The crystal structure is characterized by C-H⋯N hydrogen bonds. The crystal packing also exhibits π-π inter-actions, with a centroid-centroid distance of 3.6348 (15) Å.

Related literature

For biological properties of triazolothia­diazines, see: Feng et al. (1992 ▶); Mohan & Anjaneyalu (1987 ▶); Holla et al. (2001 ▶); Walser et al. (1991 ▶); Hirota et al. (1991 ▶); Bradbury & Rivett (1991 ▶); Heindel & Reid (1980 ▶); Heidelberger et al. (1957 ▶). For related structures, see: Andersson & MacGowan (2003 ▶); Novak et al. (2006 ▶).

Experimental

Crystal data

C12H11FN4S

M = 262.31

Monoclinic,

a = 13.322 (3) Å

b = 13.017 (3) Å

c = 7.1912 (16) Å

β = 105.308 (4)°

V = 1202.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.770, T max = 1.000

11097 measured reflections

2119 independent reflections

1828 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.06

2119 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202185X/bt5922sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202185X/bt5922Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202185X/bt5922Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H11FN4S	F(000) = 544
Mr = 262.31	Dx = 1.449 Mg m−3
Monoclinic, P21/c	Melting point: 455 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.322 (3) Å	Cell parameters from 2119 reflections
b = 13.017 (3) Å	θ = 2.2–25.0°
c = 7.1912 (16) Å	µ = 0.27 mm−1
β = 105.308 (4)°	T = 293 K
V = 1202.8 (4) Å3	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	2119 independent reflections
Radiation source: fine-focus sealed tube	1828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.770, Tmax = 1.000	k = −15→15
11097 measured reflections	l = −8→8

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.4632P] where P = (Fo2 + 2Fc2)/3
2119 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.50854 (4)	0.90687 (4)	0.19250 (9)	0.0542 (2)
F1	0.05432 (12)	1.31988 (11)	−0.1252 (2)	0.0845 (5)
N1	0.37247 (14)	0.64191 (13)	0.1417 (3)	0.0511 (5)
N2	0.46299 (14)	0.70215 (13)	0.1828 (3)	0.0550 (5)
N3	0.32718 (12)	0.80332 (11)	0.1211 (2)	0.0397 (4)
N4	0.26399 (12)	0.88834 (12)	0.0605 (2)	0.0403 (4)
C1	0.28158 (17)	1.16575 (16)	0.0713 (3)	0.0534 (6)
H1	0.3526	1.1746	0.1256	0.064*
C2	0.21920 (19)	1.25088 (18)	0.0115 (4)	0.0626 (6)
H2	0.2476	1.3166	0.0253	0.075*
C3	0.11625 (18)	1.23664 (17)	−0.0673 (4)	0.0566 (6)
C4	0.07182 (18)	1.14193 (19)	−0.0911 (4)	0.0625 (6)
H4	0.0008	1.1346	−0.1464	0.075*
C5	0.13374 (16)	1.05684 (17)	−0.0319 (3)	0.0536 (6)
H5	0.1042	0.9916	−0.0479	0.064*
C6	0.24016 (15)	1.06767 (15)	0.0515 (3)	0.0407 (5)
C7	0.30545 (14)	0.97569 (14)	0.1164 (3)	0.0378 (4)
C8	0.41148 (15)	0.98739 (15)	0.2543 (3)	0.0446 (5)
H8A	0.4073	0.9702	0.3833	0.054*
H8B	0.4330	1.0586	0.2552	0.054*
C9	0.43346 (15)	0.79735 (15)	0.1685 (3)	0.0436 (5)
C10	0.29301 (15)	0.70301 (14)	0.1038 (3)	0.0423 (5)
C11	0.18178 (17)	0.67302 (16)	0.0591 (4)	0.0547 (6)
H11A	0.1431	0.7122	−0.0514	0.066*
H11B	0.1548	0.6907	0.1677	0.066*
C12	0.1639 (2)	0.56042 (18)	0.0163 (4)	0.0671 (7)
H12A	0.1819	0.5441	−0.1011	0.101*
H12B	0.0920	0.5443	0.0024	0.101*
H12C	0.2066	0.5210	0.1204	0.101*

	U11	U22	U33	U12	U13	U23
S1	0.0360 (3)	0.0450 (3)	0.0800 (4)	−0.0006 (2)	0.0126 (3)	0.0070 (3)
F1	0.0731 (10)	0.0583 (9)	0.1191 (13)	0.0317 (8)	0.0204 (9)	0.0218 (8)
N1	0.0518 (11)	0.0354 (9)	0.0640 (12)	0.0038 (8)	0.0113 (9)	−0.0002 (8)
N2	0.0464 (10)	0.0411 (10)	0.0745 (13)	0.0081 (8)	0.0108 (9)	0.0033 (9)
N3	0.0371 (8)	0.0311 (8)	0.0479 (9)	0.0031 (7)	0.0060 (7)	0.0004 (7)
N4	0.0357 (9)	0.0329 (9)	0.0489 (10)	0.0036 (7)	0.0053 (7)	−0.0006 (7)
C1	0.0437 (12)	0.0385 (12)	0.0739 (15)	0.0028 (9)	0.0084 (10)	0.0023 (10)
C2	0.0622 (15)	0.0361 (12)	0.0880 (18)	0.0041 (11)	0.0175 (13)	0.0021 (11)
C3	0.0581 (14)	0.0450 (13)	0.0682 (15)	0.0194 (11)	0.0194 (11)	0.0112 (11)
C4	0.0413 (12)	0.0615 (15)	0.0780 (16)	0.0107 (11)	0.0039 (11)	0.0074 (13)
C5	0.0426 (12)	0.0425 (12)	0.0702 (15)	0.0008 (9)	0.0049 (10)	0.0036 (10)
C6	0.0404 (11)	0.0367 (10)	0.0443 (11)	0.0030 (8)	0.0099 (9)	0.0008 (8)
C7	0.0364 (10)	0.0350 (10)	0.0414 (10)	−0.0004 (8)	0.0091 (8)	0.0005 (8)
C8	0.0394 (11)	0.0332 (10)	0.0550 (12)	−0.0019 (8)	0.0013 (9)	−0.0002 (9)
C9	0.0383 (10)	0.0400 (11)	0.0511 (12)	0.0050 (9)	0.0091 (9)	0.0035 (9)
C10	0.0483 (11)	0.0312 (10)	0.0446 (11)	0.0006 (9)	0.0071 (9)	−0.0015 (8)
C11	0.0498 (13)	0.0416 (12)	0.0682 (14)	−0.0055 (10)	0.0075 (11)	−0.0017 (10)
C12	0.0722 (17)	0.0486 (13)	0.0808 (17)	−0.0161 (12)	0.0210 (14)	−0.0076 (12)

S1—C9	1.724 (2)	C4—C5	1.379 (3)
S1—C8	1.809 (2)	C4—H4	0.9300
F1—C3	1.359 (2)	C5—C6	1.393 (3)
N1—C10	1.294 (2)	C5—H5	0.9300
N1—N2	1.403 (2)	C6—C7	1.481 (3)
N2—C9	1.296 (2)	C7—C8	1.504 (3)
N3—C9	1.368 (3)	C8—H8A	0.9700
N3—C10	1.377 (2)	C8—H8B	0.9700
N3—N4	1.389 (2)	C10—C11	1.483 (3)
N4—C7	1.282 (2)	C11—C12	1.504 (3)
C1—C6	1.383 (3)	C11—H11A	0.9700
C1—C2	1.384 (3)	C11—H11B	0.9700
C1—H1	0.9300	C12—H12A	0.9600
C2—C3	1.351 (3)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12C	0.9600
C3—C4	1.359 (3)
C9—S1—C8	94.03 (9)	N4—C7—C8	123.28 (17)
C10—N1—N2	108.10 (16)	C6—C7—C8	119.81 (16)
C9—N2—N1	106.96 (17)	C7—C8—S1	112.80 (14)
C9—N3—C10	105.32 (16)	C7—C8—H8A	109.0
C9—N3—N4	128.67 (16)	S1—C8—H8A	109.0
C10—N3—N4	124.63 (15)	C7—C8—H8B	109.0
C7—N4—N3	115.66 (15)	S1—C8—H8B	109.0
C6—C1—C2	121.1 (2)	H8A—C8—H8B	107.8
C6—C1—H1	119.4	N2—C9—N3	110.27 (17)
C2—C1—H1	119.4	N2—C9—S1	128.82 (16)
C3—C2—C1	118.7 (2)	N3—C9—S1	120.86 (14)
C3—C2—H2	120.6	N1—C10—N3	109.33 (17)
C1—C2—H2	120.6	N1—C10—C11	126.78 (18)
C2—C3—C4	122.5 (2)	N3—C10—C11	123.81 (17)
C2—C3—F1	119.1 (2)	C10—C11—C12	113.32 (19)
C4—C3—F1	118.4 (2)	C10—C11—H11A	108.9
C3—C4—C5	119.0 (2)	C12—C11—H11A	108.9
C3—C4—H4	120.5	C10—C11—H11B	108.9
C5—C4—H4	120.5	C12—C11—H11B	108.9
C4—C5—C6	120.6 (2)	H11A—C11—H11B	107.7
C4—C5—H5	119.7	C11—C12—H12A	109.5
C6—C5—H5	119.7	C11—C12—H12B	109.5
C1—C6—C5	118.08 (19)	H12A—C12—H12B	109.5
C1—C6—C7	121.91 (18)	C11—C12—H12C	109.5
C5—C6—C7	120.01 (18)	H12A—C12—H12C	109.5
N4—C7—C6	116.73 (16)	H12B—C12—H12C	109.5
C10—N1—N2—C9	0.3 (2)	N4—C7—C8—S1	46.9 (2)
C9—N3—N4—C7	−26.4 (3)	C6—C7—C8—S1	−138.27 (16)
C10—N3—N4—C7	168.98 (18)	C9—S1—C8—C7	−49.59 (16)
C6—C1—C2—C3	−0.1 (4)	N1—N2—C9—N3	0.5 (2)
C1—C2—C3—C4	−0.4 (4)	N1—N2—C9—S1	−177.06 (16)
C1—C2—C3—F1	179.6 (2)	C10—N3—C9—N2	−1.0 (2)
C2—C3—C4—C5	0.3 (4)	N4—N3—C9—N2	−167.93 (18)
F1—C3—C4—C5	−179.7 (2)	C10—N3—C9—S1	176.72 (15)
C3—C4—C5—C6	0.2 (4)	N4—N3—C9—S1	9.8 (3)
C2—C1—C6—C5	0.6 (3)	C8—S1—C9—N2	−156.4 (2)
C2—C1—C6—C7	−179.4 (2)	C8—S1—C9—N3	26.27 (18)
C4—C5—C6—C1	−0.6 (3)	N2—N1—C10—N3	−1.0 (2)
C4—C5—C6—C7	179.3 (2)	N2—N1—C10—C11	−177.8 (2)
N3—N4—C7—C6	179.22 (16)	C9—N3—C10—N1	1.2 (2)
N3—N4—C7—C8	−5.8 (3)	N4—N3—C10—N1	168.80 (17)
C1—C6—C7—N4	−167.62 (19)	C9—N3—C10—C11	178.14 (19)
C5—C6—C7—N4	12.5 (3)	N4—N3—C10—C11	−14.3 (3)
C1—C6—C7—C8	17.2 (3)	N1—C10—C11—C12	−13.0 (3)
C5—C6—C7—C8	−162.73 (19)	N3—C10—C11—C12	170.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2i	0.93	2.51	3.428 (3)	172
C8—H8A···N1ii	0.97	2.50	3.410 (3)	156
C8—H8B···N2i	0.97	2.30	3.228 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2i	0.93	2.51	3.428 (3)	172
C8—H8A⋯N1ii	0.97	2.50	3.410 (3)	156
C8—H8B⋯N2i	0.97	2.30	3.228 (3)	160

Symmetry codes: (i) ; (ii) .